The Activity You Should Always Include in a Toddler-Friendly Itinerary

Why Kathryn Beard of Moms Know Best makes sure there's playground time everywhere she goes with her two toddlers.

Every month, I’ll be bringing you interviews from travel experts/caregivers from around the globe as part of Travel with Toddlers—because as we all know, every! kid! is! different! I want to include a wide range of voices here, so if you or someone you know would like to be featured, comment/reply and let me know. Thank you for reading Travel with Toddlers! If you like my work, please consider subscribing or buying me a coffee. Any bit is appreciated. Now, on to the good stuff! ❤️

I’m a big believer in rhythms over schedules. Even as my toddler has dropped naps (send help!) we are still following almost the same rhythms as when they first arrived: Meal—>Play—>Rest.

One of the reasons travel can be so challenging is that it naturally throws us off our equilibrium. I can generally stuff any crabiness or hangry moments way down in favor of exploring a new place or trying something new, but my toddler? That’s what sets you up for a meltdown.

That’s why I always plan out a vacation rhythm. It can take a few days to settle into it, but the more I can mimic our usual rhythm (okay, schedule) the more likely we’ll all enjoy our time together. It adds the structure my toddler needs without making it feel like every day is exactly the same, since newness is one of my favorite parts of travel.

Part of this is planning a really smart itinerary. That’s why I’m so excited to bring Kathryn Beard on today from The Moms Know Best, which is one of my FAVORITE newsletters.

Kathryn Beard on Travel with Toddlers

Her newsletter is so useful because she’s right in the thick of it with me: Parenting two kiddos (8 months, 3.5 years) in Alexandria, VA, a suburb of Washington, D.C. No matter what the topic is, I manage to learn something new—and I find with toddlers, sometimes the smallest “hacks” like a quick script to stave off a meltdown or a quiet, easy craft setup has the best payoff.

Here’s how Kathryn travels with her two little ones:¹

Do you travel often? What’s your travel “style” before and after kids?

Before kids, my husband and I had the Southwest Companion Pass and would frequently jet off for quick weekend getaways. My travel style was research and plan absolutely everything. My family would make fun of me for my elaborate Google Docs and Powerpoint presentations for every vacation. (Editor’s note: My love language!!) I was also “Team Carry On Only” and I take great pride that I packed for my two-week Italian honeymoon in the small Away suitcase.

Not any more! After having kids, we travel much less. Maybe one trip a season and I am “Team pack everything.” My days of being a light packer are over. I’d rather overpack and check a bag so the kids have a few comforts from home to make sleep, eating, and playtime easier.

What’s your top piece of advice for traveling with kids?

My #1 travel tip for families with kids is: Find the playgrounds. It sounds simple, but we’ve had many long travel days saved by finding a playground to let my toddler get out energy. I love the app Playground Buddy. It’s a free app that lets you search around your location to find where all the playgrounds are nearby. It also lists the amenities each one has so you can find one with a bathroom if you need. On our four-hour drive to the beach last summer with a newborn and a 3-year-old, we found this amazing playground through the app that we would have never found otherwise where my toddler ran around for an hour while I fed and changed the baby.

I’ve found that a toddler will tolerate a more “boring” activity if a trip to a playground is promised in the future. In Portland, Oregon, last year, the Rose Garden was not holding her interest, but there was this great playground nearby where we spent an hour afterwards. Also, I am constantly baffled why rest stops on highways don’t have playgrounds! That would make road trips so much easier.

We’re told babies are more portable, but it’s not as easy as that. What’s your baby travel advice?

Four to five months is the travel sweet spot and I wish we had taken more advantage of it. We took one trip with my second child during this time to visit friends in Naples, Florida and it was so easy with the baby. It made me regret not planning something else during that magic window.

At that age, they are starting to get more on a schedule and are sleeping for longer stretches, but they are still not crawling yet and haven’t started solid food yet. So you can really just tote them around and they will largely just nap in a carrier or the stroller. When we say babies are more portable, that’s the age we’re really talking about.

What about for toddlers?

My travel mantra is the juice is always worth the squeeze. Long travel days with toddlers can be hard. We did a big trip last summer to Oregon to visit family. The travel day to get there involved a 3 a.m. wakeup, two flights, a long layover in Chicago, and then a two-hour-drive once we got to Oregon. It was one of the longest days of my life spent trying to keep a grumpy and overtired two-year-old entertained and happy. But we survived and made it to Astoria, Oregon where my toddler proceeded to have the most magical week. Give yourself lots of grace on travel days, use screens if you need, throw most of your parenting rules out the window, and survive. The final destination is usually worth it.

And this one I learned the hard way, but always remember to pack toddler-approved snacks for the way home in your suitcase. It’s great to have tons of snack options for the flight or car ride to your destination, but everyone always forgets about the trip home. I always pack a Ziploc bag of some pre-packaged non-meltable bars and crackers in my suitcase for the way home.

The best place to travel with babies and toddlers is…

We spend a week each summer in Cape Charles, Virginia which is an under-the-radar beach destination four hours from Washington, D.C. on the Eastern Shore of Virginia. It’s an amazing place for families. The beach is lovely and the water is shallow for little kids. Everyone drives golf carts around the town which is so much fun. And the town is this quaint, historic town with cafes, ice cream shops, and boutiques, but doesn’t have the crowds of many East Coast beaches.

The best hotel for babies and toddlers is…

It feels cliche to name a hotel at Disney World, which is a place very much geared towards kids, but we had an amazing time last fall when we stayed at the Yacht Club. All Disney hotels are kid-friendly, but the Yacht Club’s amazing pool with a sand bottom and shallow “beach” area make it an especially great choice for families with little kids. It is also nice to be walking distance to two parks (it allowed someone to come home easily with the toddler for nap time) and my toddler thought riding the nearby Skyliner was more fun than any rides in the parks.

(Editor’s note: I think what Disney haters don’t understand is there’s so much psychological safety there for parents, like you just know there’s not going to be some dumb logistical issue at this hotel that creates a meltdown, and that’s worth it to me!)

The top pieces of gear that Kathryn doesn’t leave home without…

Ensuring my kids sleep well on vacations has always been a top priority. Even though it’s annoying to pack them, we’ve always traveled with all of our own sleeping gear verses renting anything or using a hotel’s pack and play to ensure they can sleep in something they are used to.

We are huge fans of the Guava travel crib with a Slumberpod over it for little kids. And now, my toddler uses the Hiccapop blow up mattress.

We also always travel with strollers. They make getting through airports so much easier. When we had just one child, we used the Nuna Trvl stroller and loved it. Now that we have two kids, we upgraded to the UppaBaby Minu Double stroller and are big fans. We did splurge on the travel case for it and it gives me peace of mind when we check it.

What’s your best travel memory so far?

Traveling with small children can be hard and yes it does sometimes feel like you are just parenting in another location without your routine or all of your things. I asked my husband for a travel tip he would share for these questions and he said, “Wait until they are older.” 🤦🏼‍♀️ BUT despite that, some of my best parenting memories are watching my girls experience new things.

On our Disney trip, the sheer joy she experienced as we drove by a Disney bus with Elsa on the side of it. She screamed, “ELSA’s ON A BUS!” We still laugh about that today. We spent so much money to take her to Disney and her takeaway memory is that she saw a bus with her favorite princess on it. A good reminder for all of us that joy can be found in the smallest of things. ❄️

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Thank you, Kathryn! I love that bus story so much. That was certainly my toddler’s highlight at Disney the first time we went, as we are but small town folk and never get to ride buses and monorails and trains. I think sometimes we forget as parents that everything is new and so we expect the big-ticket items to be the most exciting when, like, there’s a duck and that’s the best thing ever.

On to this week’s recs:

This week’s rapid-fire recs.

Disclosure: This newsletter contains affiliate links, meaning I get a commission if you decide to make a purchase through my links, at no cost to you. I promise I’ll only ever recommend products I’ve actually used and loved.

1. I don’t know if this snow is ever going to melt; in the meantime, I bookmarked these recs from Kathryn.

2. We have taken to “trash building” at our house—I collect cardboard and other scraps from the recycling bin and my toddler just goes to town with this tape.

3. For points people, Hyatt just did a major devaluation (thanks for the heads up, The Point | Rachel Lipson!)

4. Forget the Survivor winners, what about the first boots? (NYT Gift Link)

5. S/O to my friend Shannon for sending me this Vermont hot chocolate crawl.

Thanks for being here.

“Find the playgrounds” is one of the best pieces of advice I was given before our first toddler roadtrip. Babies need to stop every hour or so for feeding and changing and so on but toddlers? They gotta wiggle.

At this point some of our favorite travel memories are playground-related. In Portland, ME, the Eastern Promenade Playground overlooks the ocean to a stunning view, and if you time it right, the Gelato Fiasco food truck is at the bottom of the hill. Now my toddler proudly asks if “we’ll be stopping at my favorite playground” each time we drive to visit family there.

A summer dream,

Kayla

Thank you for supporting Travel with Toddlers! If you liked this issue, please like it, share it, subscribe, or you can buy me a coffee. It really does mean a lot. I’m just a mom in the thick of the toddler years trying to create core memories for our whole family while minimizing meltdowns—I sincerely hope this helps you do the same.

1. This interview has been lightly edited for clarity and brevity.